Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors

Ligaya M. Simpkins, Scott Bolton, Zulan Pi, James C. Sutton, Chet Kwon, Guohua Zhao, David R. Magnin, David J. Augeri, Timur Gungor, David P. Rotella, Zhong Sun, Yajun Liu, William S. Slusarchyk, Jovita Marcinkeviciene, James G. Robertson, Aiying Wang, Jeffrey A. Robl, Karnail S. Atwal, Robert L. Zahler, Rex A. ParkerMark S. Kirby, Lawrence G. Hamann

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

The synthesis and structure-activity relationships of novel dipeptidyl peptidase IV inhibitors replacing the classical cyanopyrrolidine P1 group with other small nitrogen heterocycles are described. A unique potency enhancement was achieved with β-branched natural and unnatural amino acids, particularly adamantylglycines, linked to a (2S,3R)-2,3-methanopyrrolidine based scaffold.

Original languageEnglish
Pages (from-to)6476-6480
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number23
DOIs
StatePublished - 1 Dec 2007

Keywords

  • DPP4
  • Diabetes
  • GLP-1
  • Non-nitrile
  • Serine protease

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    Simpkins, L. M., Bolton, S., Pi, Z., Sutton, J. C., Kwon, C., Zhao, G., Magnin, D. R., Augeri, D. J., Gungor, T., Rotella, D. P., Sun, Z., Liu, Y., Slusarchyk, W. S., Marcinkeviciene, J., Robertson, J. G., Wang, A., Robl, J. A., Atwal, K. S., Zahler, R. L., ... Hamann, L. G. (2007). Potent non-nitrile dipeptidic dipeptidyl peptidase IV inhibitors. Bioorganic and Medicinal Chemistry Letters, 17(23), 6476-6480. https://doi.org/10.1016/j.bmcl.2007.09.090